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CAS No. : | 848328-57-4 | MDL No. : | MFCD24496597 |
Formula : | C12H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYOFPRGAVPMDRY-UHFFFAOYSA-N |
M.W : | 206.24 | Pubchem ID : | 22325151 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5-amino-2-bromopyrazine; 2-((benzyloxy)methyl)cyclopropanecarboxylic acid With pyridine In acetonitrile at 2℃; for 0.0833333h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 24.5h; | Intermediate 9 2-((benzyloxy)methyl)-N-(5-bromopyrazin-2- yl)cyclopropanecarboxamide [0110] A mixture of 2-((benzyloxy)methyl)cyclopropanecarboxylic acid (1 138 mg, 5.52 mmol), 5-bromopyrazin-2-amine (800 mg, 4.60 mmol), and pyridine (1125 μ, 13.79 mmol) were dissolved in anhydrous acetonitrile (6568 μ). The reaction stirred at room temperature for 5 minutes, followed by addition of propylphosphonic anhydride solution (50 wt % in EtOAc) (5469 μ, 9.20 mmol) over the course of 30 minutes. The reaction continued stirring for 24 hours, then was concentrated in vacuo to afford as residue which was purified via normal phase column chromatography using an isocratic gradient of 5% MeOH/DCM on the Teledyne ISCO CombiFlashTM Purification system to afford the title compound as a dark yellow/brown solid which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85 - 0.98 (m, 1 H) 1.03 - 1.13 (m, 1 H) 1.52 - 1.70 (m, 1 H) 1.97 - 2.07 (m, 1 H) 3.43 - 3.63 (m, 2 H) 4.43 - 4.53 (m, 2 H) 7.24 - 7.40 (m, 5 H) 8.56 - 8.64 (m, 1 H) 9.12 (d, J=1.26 Hz, 1 H) 1 1.23 - 1 1.33 (m, 1 H). ESI-MS: m/z [M + H]+ 362.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pyridine / acetonitrile / 0.08 h / 2 °C 1.2: 24.5 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,4-dioxane / 1 h / 100 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / toluene / 0.33 h / Cooling with ice 1.2: 2 h / 100 °C 2.1: sodium hydroxide / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.1 g | With sodium hydroxide In methanol at 20℃; | 5.2 2. Synthesis of Compound 3.1c Compound 3.1b (9.37 g, 0.04 mol) was dissolved in 20 mL of methanol.A 2.5 N sodium hydroxide solution was added and the reaction was stirred at room temperature.After the reaction was completed, the pH was adjusted to about 3 with 1N hydrochloric acid and extracted with dichloromethane.The organic phase obtained was dried over anhydrous sodium sulfate, filtered and evaporated.The title product 3.1c (8.1 g, colorless oil) was obtained.The product was directly subjected to the next reaction without purification. |
1196mg | With water; sodium hydroxide In ethanol at 70℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.8 g | Stage #1: 2-((benzyloxy)methyl)cyclopropanecarboxylic acid With oxalyl dichloride In tetrahydrofuran at 20℃; for 0.5h; Cooling with ice; Stage #2: With sodium azide In tetrahydrofuran; water | 5.3 3. Synthesis of compound 3.1d Compound 3.1c (6.19 g, 0.03 mol) was dissolved in 20 mL of tetrahydrofuran.Oxalyl chloride (4.57 g, 0.036 mol) was added dropwise under ice bath.After the addition was completed, stirring was continued for 0.5 h at room temperature.The above tetrahydrofuran solution was added dropwise to a solution of sodium azide (2.93 g) in water (2 mL).After completion of the reaction, it was extracted with dichloromethane, and the obtained organic phase was washed three times (30 mL each time).The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The title product 3.1d (6.8 g, colorless oil) was obtained.The product was directly subjected to the next reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice 2: toluene / 4 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dirhodium tetraacetate / diethyl ether / 22 h / 25 - 30 °C 2: sodium hydroxide; water / ethanol / 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C 3: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
685mg | With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 2h; |
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